Help Desk: Your Turn!

I've had three requests in the last few weeks for which I just don't have good answers. And that's where you come in! I'll post the questions- You help with answers in the comments. An interactive help desk! Woo hoo!

Question number one:

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My husband is wanting to update his look, and he's asked if I'll help. I'm wondering about the best places to find menswear that is slightly trendy but not metro. As an extra challenge, I need to find items that don't wrinkle easily, because my husband often travels for business.

Question number two:

Do you ever feature clothing for larger women? I'm not talking plus size just larger sizes. I'm short and fat (no getting around it) and I don't know how some of the clothes you show would work on me. I don't shop much because its not fun, but I do enjoy looking at the clothes you show.Any shopping sites you can recommend?

Question number three:

(Paraphrased because I can't find the original e-mail). I want to have a family portrait done, but I don't like that matchy-matchy look. Any ideas on how I can tie our looks together without looking silly? If you have any examples of family portraits you've loved from photographers' websites, I'd love to see them!